Water → 4'-Formyl-[1,1'-biphenyl]-2-carbonitrile

HRID 397123Notes

Reaction equation

HRID 397123 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]#[N:12])=[CH:5][CH:4]=1.C(=O)(O)[O-:18].[Na+].O>CS(C)=O>[CH:2]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]#[N:12])=[CH:5][CH:4]=1)=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 15019124'-(Bromomethyl)-2-cyanobiphenyl

Product 1

HCID 13940624'-Formyl-[1,1'-biphenyl]-2-carbonitrileYield 63.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-(4-bromomethylphenyl)benzonitrile (12 g) and sodium bicarbonate (26 g) in dimethyl sulfoxide (150 ml) was heated at 120° C. for 5 hours with stirring. After addition of water, the mixture was extracted with ethyl acetate. The extract was washed with water, dried and concentrated to dryness. The residue was purified by column chromatography on silica gel to give crystals. Recrystallization from chloroform-isopropyl ether gave colorless needles (5.77 g, 63%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by column chromatography on silica gel
  6. customto give crystals
  7. customRecrystallization from chloroform-isopropyl ether

Sources & evidence

ORD record
ord-68667db1d63a446f9b932870d79a2476
Source dataset
uspto-grants-2003_08
Patent number
US06608210B2

Reaction notes

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